Mycoskie sold his online driver education company for $500,000 to finance Toms shoes. The company name is derived from the word "tomorrow", and evolved from the original concept, "Shoes for Tomorrow Project". Mycoskie initially commissioned Argentine shoe manufacturers to make 250 pairs of shoes. Sales officially began in May 2006. After an article ran in the Los Angeles Times, the company received order requests for nine times the available stock online, and 10,000 pairs were sold in the first year. The first batch of 10,000 free shoes were distributed in October 2006 to Argentine children.
Toms' business model is known as the "one for all concept" model, which is referring to the company's promise to deliver a pair of free shoes to a child in need for every sale of their retail product. The countries involved have included Argentina, Ethiopia, Guatemala, Haiti, Mexico, Rwanda, South Africa and the United States. The business has grown beyond producing shoes and has included eyewear and apparel in Toms product lines. The company uses word-of-mouth advocacy for much of its sales, centering its business focus on corporate social responsibility. Part of this model originally involved a non-profit arm called "Friends of Toms" that recruited volunteers to help in the shoe distributions in foreign countries. Toms trademarked the phrase "One for One" to describe its own business model. Toms has received criticism from the international development community  who have stated that Toms' model is designed to make consumers feel good rather than addressing the underlying causes of poverty. Criticisms have also included whether or not the shoe donation is as effective as a monetary donation to other charities. Toms responded to this criticism by moving 40% of its supply chain for shoe donation to countries they actively give in. Toms presently manufactures shoes in Kenya, India, Ethiopia and Haiti.
In June 2014, the company announced that Mycoskie was looking to sell part of his stake in the company to help it grow faster and meet its long-term goals. On August 20, 2014 Bain Capital acquired 50% of Toms. Reuters reported that the transaction valued the company at $625 million; Mycoskie's personal wealth following the deal was reported at $300 million. Mycoskie retained 50% ownership of Toms, as well as his role as "Chief Shoe Giver". Mycoskie said he would use half of the proceeds from the sale to start a new fund to support socially minded entrepreneurship, and Bain would match his investment and continue the company's one-for-one policy.